Gossip Grease
by Where's Waldorf
Summary: Basically, the Grease plot in the world of Gossip Girl. Nate as Zuko, Jenny as Sandy, Chuck as Kenickie and Blair as Rizzo. Sounds ridiculous but it actually matches in a fun way! Give it a try. Pairings include heavy Chair and Nenny, with Derena in the background.
1. Chapter 1

**I don't own Gossip Girl or Grease. But I wouldn't mind owning Ed Westwick.**

**So I don't know about anyone else, but I always loved Rizzo and Kenickie's story way more than the Danny and Sandy story. I'm more invested in Chair too so I write them more properly and analytically. S****o that's why I've listed Chair as the pairing****. However, I am doing the whole story-line of Grease, so Nenny will still get a lot of long moments too. This first chapter introduces everyone and the only pairing we really see is Nate and Jenny. Enjoy! :)**

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_It was the end of summer and it was a beautiful day. Not just because of the perfect weather and the gorgeous beach atmosphere, but because of the love that had grown between Nathaniel Archibald and Jennifer Humphrey. The pair had spent the day laughing, taking pictures, building sandcastles and swimming. They were currently embracing as they watched the sunset from their private little area on the beach. They turned to face each other at the same time and kissed passionately._

_"I'm going back to Hudson, I might never see you again" Jenny cried after they parted, her blue eyes filled with sadness._

_"Don't talk that way Jenny" Nate replied with a soft smile._

_"But it's true, I've just had the best summer of my life and now I have to go away. It isn't fair," she said glumly, looking down. Nate tipped her chin up and looked her deeply in the eyes before pressing his lips to hers. He wrapped his hand around her neck tightly as he forcefully kissed her. _

_Jenny whimpered as she struggled to break free from his onslaught. _

_"Nate don't spoil it" she gasped out once she escaped his lips._

_"It's not spoiling it Jenny, it's only making it better" he said firmly with a warm look in his eyes as he held her shoulders._

_"Nate, is this the end?" Jenny asked softly, running her hands on his chest._

_"Of course not," he answered with a little laugh, "it's only the beginning."_

Present

It was the first day back at school for Constance and St Jude's.

Daniel Humphrey was lugging his bag on one shoulder as he headed to the front gate of St Jude's, when suddenly he was knocked into by a group of lacrosse players, causing him to drop his bag and send all of its contents flying. Dan looked back to see them all continuing to walk as though they hadn't seen him at all. He sighed, used to being invisible, and crouched down to pick up all of his items off the floor. Dan reached for his tuna fish sandwich when a pair of designer shoes came into his vision.

He looked up to see none other than Chuck Bass smirking down at him, scarf and all. Dan picked up the brown paper bag that contained his sandwich and stood up. Chuck wrinkled his nose as he stared at Dan.

"You're not supposed to eat that, you're supposed to bury it" Chuck said, motioning to the sandwich.

"That's a homemade lunch" Dan retorted, and Chuck raised his eyebrows in amusement.

"Your lame 90's Dad dragged his ass out of bed for you?" Chuck snorted.

"Shut up, he does it every year on the first day of school" Dan muttered.

"Big deal" Chuck replied sarcastically, before lighting up a cigarette and glaring at a freshman boy that walked past.

Chuck and Dan did not see eye to eye, mostly due to Chuck's snobbery and Dan's distaste for Chuck's lifestyle. However Dan had fallen onto Chuck's radar when Chuck's father, Bart Bass, had asked Dan to tutor him last year. Chuck was insulted to say the least, making the whole thing an utter pain for Dan. Dan gave up half an hour into the session and Chuck, feeling bored, suggested they get drunk. They ended up going to a bar, getting into a fight and then arrested. After sharing such an experience, they had a secret, begrudging respect for each other.

"So, where were you all summer?" Dan asked.

"What are you, my mother?" Chuck drawled.

"I was just asking" Dan said raising his hands in the air.

"I was working, which is more than you can say Humphrey" Chuck said smugly.

"Working?" Dan asked disbelievingly of the spoilt playboy.

"That's right, I was interning at Bass Industries moron" Chuck sneered.

"Sounds like a fun summer" Dan replied sarcastically.

"Eat me. I'm trying to convince my Dad to get me my own limo" Chuck explained, taking another drag from his cigarette. Dan nodded, somehow used to the obscenely expensive demands of the kids that went to his high school.

"Want to hear what I did?" Dan asked.

"No" Chuck said, walking off to leave Dan with his gross sandwich.

Chuck strolled through the courtyard until he spotted his best friend Nate leaning against their "getting high" wall, surrounded by Constance girls as usual. Chuck could get women easily, but he had to speak to them first. Girls just had to _see_ Nate to immediately throw themselves at him. Where Nate was the nicer hot guy, Chuck was the handsome bastard. They were both idolised by their male peers. As soon as Nate noticed Chuck, he flashed a grin and walked up to him. They shook hands and patted each other on the back as they greeted each other.

"You see any new conquests over there?" Chuck asked nodding towards the girls Nate was speaking to.

"Nah, the same old girls that everyone's made it with" Nate replied with a grin and Chuck smirked in understanding.

"So what did you do all summer Nathaniel?" Chuck asked.

"I was hanging around the beach, _you _know" Nate said, giving Chuck a sly look.

"How was the action at the beach man?" Chuck said, chuckling.

"It was crazy. I did meet this one girl who was sort of cool" Nate said with a smile, unconsciously scratching his neck as he tried to be casual about it.

"Did she put out?" Chuck asked with an evil grin.

"Oh come on Chuck, is that all you can think about?" Nate exclaimed, laughing.

"I'm Chuck Bass" he replied, matter-of-factly.

Nate shook his head and rolled his eyes, before patting his friend on the back as they walked to class together.

On the other side of the courtyard, Jenny was walking with Serena Van der Woodsen. Eric was a new friend she had made over the summer, and he had introduced her to his sister Serena who went to Constance. It had turned out that Jenny was going to stay in Brooklyn with her father and brother instead of returning to Hudson. Jenny was now being sent to a school with intimidating, rich, well-dressed girls from the Upper East Side.

"Do I look okay Serena?" Jenny asked nervously, pulling at her uniform.

"Sure, you look good" Serena replied brightly.

"I'm really nervous, you know" Jenny said.

"You look terrific" Serena reinforced with a smile.

"So, this is Constance?" Jenny sighed, looking around.

"Yep, you'll love it" Serena said, ever the peppy blonde.

"I loved the last school I was at, I wish I was there right now" Jenny said gloomily, "still, I'm no stranger to heartbreak."

"Why? You got psoriasis?" Serena asked seriously. Jenny gave her a confused look and Serena giggled, pulling her along.

Blair Waldorf strutted into the school, followed by her gang of minions.

"Oh God," she sighed under her breath as she took in her personal kingdom.

"Well, here we are again" she announced drily to the girls trailing behind her.

"Yeah, but this time we're seniors" Iz said excitedly.

"And I'm going to rule the school" Blair said with a confident smile and the girls giggled in response, nodding their heads.

"Ladies, that giggling is so adolescent" Blair snapped coldly when they started to carry on.

"We _are_ adolescent" Kati replied.

"We don't have to flaunt it" Blair said haughtily, before continuing, "Okay girls, let's go get them."

Blair marched on with a fierce look in her eyes, a self-satisfied smile and a sway in her hips. Her minions clambered to do the same as they trailed behind her.

Jenny went to the office of the joint schools to collect her class lists. She entered to find all the teachers rushing to pick up their class rosters for the semester.

"I've got Bass again" Mr Pieser exclaimed with a long suffering sigh.

"He's been here longer than I have" Headmistress Queller responded in understanding, before spotting Jenny.

"May I help you dear?"

"Oh, yes, this is my first day of school and I'm not really sure where I'm supposed to be" Jenny stuttered.

"Welcome to Constance, you'll first have to fill out a few of these forms" she said kindly, handing Jenny 10 pages to fill out. The bell rang and Jenny winced, knowing she was going to be late for her first class.

Everyone was in homeroom listening to the announcements being made by Headmistress Queller over the speaker. It was mostly boring updates, until some exciting news caught a lot of people's attention, but mainly Blair's.

"As you all know, we will have press covering the Snowflake Ball this year. It's our chance to show New York what fine, bright, clean-cut, wholesome students we have here at Constance and St Jude's" the principal stated. Blair had a gleam of excitement in her eye as she listened to this. It was her chance to show the world what kind of life she was going to lead outside of high school.

When it became lunchtime, Blair and her minions took their usual place on the steps of the Met.

"Did you guys get a look at Nate Archibald this morning? Looking pretty good this year, huh Blair?" Penelope said in a suggestive tone.

"That's ancient history" Blair replied, rolling her eyes. Dating Nate was mainly for show so that she could claim her throne and be on top of every girl there. Blair never gave her heart fully to any boy she dated, or anything else she might add. Her virginity was sacred to her, which was partially why Nate gave up easily.

"Well history sometimes repeats itself" Is said lightly.

Blair shrugged her shoulders nonchalantly and waved them off as she spotted her best friend, Serena walking towards them, a younger, blonde girl following her.

"Hi guys" Serena exclaimed with a smile.

"Hi S" the girls chorused.

"This is Jenny Humphrey," Serena said, before introducing all the girls sitting on the steps.

"She just moved here from Hudson" Serena informed everyone.

"Mm and how are things in...Hudson?" Blair said with a snobby, fake smile.

"Fine, thanks" Jenny replied uncomfortably. She was dressed so plainly in her uniform compared to the other girls, who had added designer accessories and headbands. Jenny could already feel the divide. Sensing the uncomfortableness, Serena changed the direction of the conversation.

"Kati, are those new glasses?"

"Oh yes, just got them for school. Don't you think they make me look smarter?"

"No, you can still see your face" Blair cut in with a smirk. Jenny swallowed, not used to such a confidently mean person.

"How do you like school so far Jenny?" Hazel asked.

"It's different" Jenny said quietly.

"Hi girls" a voice cried out from the distance.

The girls immediately groaned, recognising who it was.

"Nelly Yuki, the bad seed of Constance" Blair snarked quickly before Nelly approached them.

"Oh I just love the first day of school, don't you?" Nelly said brightly.

"It's the biggest thrill of my life" Blair replied sarcastically, but Nelly didn't pick up on the sarcasm.

"Oh you'll never guess what's happened" Nelly continued.

"Probably not" Blair said in a bored tone.

"They just announced the nominees for student council and guess who's up for vice president?" Nelly exclaimed excitedly.

"Who?" Blair asked in over exaggerated interest.

"Me! Isn't that the most? To say the least" Nelly said beaming.

"The very least" Blair drawled.

"I just hope I don't make too poor a showing" Nelly continued.

"Well, we certainly wish you the best of luck, don't we ladies?" Blair said, giving her minions a meaningful look. On cue they chorused their good luck wishes. Blair didn't like Nelly because she posed a threat to her dream of going to Yale, so she kept her as a friend to find a way to jeopardize her. However, Blair couldn't always hide her dislike for her.

"You must think I'm rude for not introducing myself, I'm Nelly Yuki" Nelly said, introducing herself to Jenny and began chattering away to her.

"B, how do you like Jenny? Do you think we could let her in to the 'Girls of the Steps'?" Serena whispered as they watched her.

"She looks too nice to be a mean girl, and did I hear Hudson?" Blair said, eyeing her out with distaste.

"What did you do this summer Jenny?" Penelope asked, building a bridge.

"Oh I spent most of it at the beach. I met a boy there."

"You spent your entire break on the beach for some guy?" Blair asked, almost rolling her eyes.

"Well he was sort of special" Jenny retorted.

"There is no such thing" Blair said coldly. Jenny shook her head ignoring Blair's comment.

"He was really romantic" she told Penelope with a sigh.

Meanwhile, Chuck and Nate were leaning against their wall smoking a joint, surrounded by a few others of their regular party crew.

"Did you see that new chick at registration? She sure beats the tissue stuffers around here" Chuck quipped with a smirk.

"You mean her boobs were bigger than Pamela's?" One guy asked in interest.

"Nobody's are bigger than Pamela's" Chuck replied with a chuckle and they all laughed.

"I want to hear about what Nate did at the beach" one of the lacrosse players said.

"Nah it was nothing" Nate replied, trying to play it off.

"Sure, _nothing_ Nathaniel, right?" Chuck teased.

"You got into her La Perla's right?" Andy Clark asked, as though he already knew the answer. The guys kept pressing and pressing Nate to tell him.

"Come on, you don't want to hear all the horny details" Nate exclaimed with a grin.

This only made them yell louder and force him further.

"Alright, I'll tell you!"

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**Next chapter should feature Chair! Review if you'd like me to continue.**


	2. Chapter 2

**Decided to insert the lyrics of the song into their dialogue. I cut them down though because I want to get to the story.**

** Another thing to keep in mind is that I have to alter what they say so it seems logical in the Upper East Side world, so for those who know the whole movie off by heart like me, be prepared to see things missing or lines replaced with something else.**

** Blair is like Rizzo but in a virginal way. She doesn't have sex with every guy, but she also doesn't lead guys on or "press against them when she dances." She's not a passionate romantic and her only focus is her social standing. I know how that her indifference to Nate seems wildly cold and unrealistic, but I don't want her to have given her heart to anyone. For now ;)**

**Also, I'm going to mix Serena's character with Jan, Frenchy and Marty's storylines, and Dan's character with Putz, Doody and Sonny's relation to their girlfriends. Chair begins at the end of this chapter. I fit them in for your enjoyment and mine ;)**

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"I had myself a blast" Nate started with a grin, all of the guys hanging on to his every word.

"It happened so fast" Jenny sighed, and the girls stopped eating to listen.

"I met a girl crazy for me."

"I met a boy, cute as could be."

"Tell me more, did you get very far?" one of the lacrosse players asked.

"Tell me more, like does he have a car?" Kati asked.

"She swam by me. She got a cramp" Nate said smugly.

"He ran by me, got my suit damp" Jenny continued, telling the story of how she met Nate.

"I saved her life, she nearly drowned" Nate continued, puffing out his chest.

"He showed off, splashing around." Jenny smiled, rolling her eyes.

"Tell me more, was it love at first sight?" Serena asked dreamily.

"Did she put up a fight?" Chuck asked with interest.

"I took her bowling in the arcade."

"We went strolling and drank lemonade" Jenny sighed as she relived the memory.

"We made out under the dock" Nate said with a cheeky grin.

"We stayed out past 10 o'clock."

"It was a summer fling, it didn't mean a thing. But those summer nights" Nate said giving the group a wink.

"Tell me more, but you don't have to brag" another guy jealously said.

"Tell me more, cause he sounds like a drag" Blair said in a bored tone, rolling her eyes.

"He got friendly, holding my hand."

"She got friendly, down in the sand."

"He was sweet, just turned 18."

"Well, she was good. You know what I mean?"

"Tell me more, how much dough did he spend?"

"Could she get me a friend?" Keith Nelson asked, and Chuck shoved him away rolling his eyes.

"It turned colder, that's where it ends" Jenny said, her smiles disappearing.

"I told her we'd still be friends."

"Then we made our true love vow."

"Wonder what she's doing now.." Nate said with a faraway look in his eyes.

"He sounds really nice" Serena said with an excited smile as they walked back to school.

"True love and he didn't lay a hand on you? Sounds like a creep to me" Blair said, ever the cynic about boys and love. She had dated Nate Archibald and he was constantly trying to have sex with her even though she never teased him with sex or led him to believe he would get it. He didn't seem to understand that his role as her boyfriend was mostly because of his reputation and not in feelings.

"Well he wasn't. He was a gentleman" Jenny said defensively.

"What was his name?" Serena asked.

"Nate. Nate Archibald."

The girls immediately burst into a fit of giggles, but Blair hit them and shut them up.

"Well, I think he sounds perfect and maybe if you believe in miracles, Prince Charming will show up again someday. Somewhere unexpected. See you later," Blair said with a huge fake smile, "come on girls."

She walked off and her minions immediately followed her, giggling.

"Do you really think so Serena?" Jenny asked hopefully.

"Sure" Serena said with a nervous smile.

"Yeah?"

"Jenny, I think I'd better get to class," she said shakily before hurrying off.

Later that night, they were all at the Kiss on the Lips party that Blair was hosting. It was a mixer between Constance and St Jude's. Blair had graciously invited Jenny, however she had a fun little plan in mind now that she knew Jenny had a fling with Nate.

Nate and a bunch of his lacrosse player friends were waiting out the front of the entry. Except for Nate, they were all acting like goofy drunks, yelling out to girls and singing.

"Guys, be cool huh?" Nate pleaded in his nice way. They immediately sobered up and stood straight silently. One of them was standing on the street and nearly got run over by a limo that pulled up.

The driver opened the door to reveal Chuck, who was approached by a grinning Nate.

"Well, what do you think?" Chuck asked with a smirk.

"The phrase over-the-top comes to mind" Nate said laughing. The others chorused in laughing, but stopped when they caught Chuck's glare.

"Wait and see Nathaniel," Chuck said smugly, "I'm bringing it everywhere from now on. Even to school."

"School?" Dan asked, suddenly joining the conversation.

"Yeah, want to make something of it?" Chuck challenged.

"I want to see you make something of this ridiculous idea" Dan continued with clear ridicule.

"You're cruising for a bruising" Chuck said, bringing his face close to Dan's and narrowing his eyes threateningly.

"Hey what is Baizen doing here? He's graduated now" Nate asked, ending Chuck and Dan's argument before it even began and Dan wandered off, leaving them.

"Think he wants to play?" Chuck said menacingly, staring Carter down.

"If he does, we're going to be ready for him" Nate said confidently.

Carter glared at them while they stared menacingly, and then seemed to change his mind about attending the party, pulling his gang away with him.

Meanwhile inside the party, Serena just rescued Jenny from being totally destroyed by a snobby couple that kept asking her questions about Hudson.

"Oh, thanks S" Jenny said in relief as Serena finished giving them the 'get lost' look.

"It's alright. You know something? You look really great" Serena said supportively, approving of her outfit choice.

"Are you sure I haven't messed up? I'm really nervous" Jenny said, laughing shakily.

"Your split dress is divine" Serena said with a grin, clutching her arm. They giggled, not noticing Blair approaching them from behind with her usual army.

"Hi Jenny" Blair said brightly.

"Oh hi Blair, hi girls" Jenny replied in a friendly tone.

"We've got a surprise for you" Blair said shortly, before heading to the exit.

"Surprise, what is it?"

"You'll see, right Blair?" Is said, before pulling Jenny along to follow Blair.

Serena tried to fix Jenny's hair slightly as they walked.

"Where are we going?" Jenny exclaimed with a laugh.

"You know, this car could be make-out city" Nate said to Chuck.

"A chick is going to have to put out before she even gets in" Keith Nelson said with a laugh.

"You'd better believe it man" Chuck drawled with a smirk.

"Hey Nate! I've got a surprise for you" Blair called out, appearing out of nowhere. All of the boys eyes lit up immediately at her appearance, especially Nate and Chuck's.

"Oh yeah?" Nate asked with a grin, thinking that she might hook up with him.

"Yeah" Blair said with a giggle, and Is thrust Jenny forward.

"Jenny?!"

"Nate?!"

"What are you doing here? I thought you were going back to Hudson?" Nate exclaimed excitedly, his eyes wide in awe.

"We had a change of plan" Jenny replied happily.

"I can't.." Nate started to say, before he noticed Chuck and the rest of the guys giving him questioning looks "that's cool baby, I mean you know how it is, rocking and rolling and what not."

"Nate?" Jenny asked, confused by his change in demeanour.

"That's my name, don't wear it out."

"What's the matter with you?"

"What's the matter with me, baby? What's the matter with you?"

The guys started laughing and grinning at Nate.

"What happened to the Nate Archibald I met at the beach?" Jenny asked, feeling hurt already.

"Well I don't know. I mean, maybe there's two of us, right? Why don't you take out a missing persons ad or try the yellow pages, I don't know?" Nate said with a fake chuckle, causing the guys behind him to laugh harder.

Jenny shook her head in disgust and disappointment.

"You're a fake and a phony and I wish that I'd never laid eyes on you" Jenny cried, humiliated, before running off. Serena chased after her immediately.

"Ooohhh" the guys all chorused.

"I wonder if she carries silver bullets" Chuck quirked.

Nate couldn't speak, the guilt eating up inside of him. He locked eyes with Blair who was smiling up at him evilly. She strutted away with her clique following, leaving Nate to deal with his friends jokes.

"So she laid her eyes on you Archibald?"

"I bet that's not all she's laid on him."

Nate started to walk off in a distracted stated.

"Archibald, I've got a car remember?" Chuck called out, stopping him.

"He was so nice to me this summer" Jenny sobbed as Serena comforted her.

"Listen, Jenny. Men are rats," Serena said, then clutched Jenny's shoulders, " Listen to me, they're fleas on rats...Worse than that! They're amoebas on fleas on rats."

Jenny giggled in between her sniffles.

"I mean they're too low for even the dogs to bite. The only man a girl can depend on is her daddy" Serena said, ignoring the voice in her head that said 'except yours.'

After Jenny had dried her tears, Serena kept talking.

"You know what you need? A night out with the girls. We're having a sleepover at my place tonight, want to come?" Serena asked.

Jenny nodded sadly.

"Good, you'll love it. Come on" Serena said putting her arm around Jenny.

Blair was having fun introducing Jenny to her evil fun at sleepovers. Firstly they had dared Kati and Is to make out. Then some of the girls began to smoke.

"Want one Jenny?" Serena asked.

"No thanks, I don't smoke" Jenny replied.

"You don't? Go ahead, try it. It won't kill you" Serena said, shoving it in her face.

Jenny inhaled and started coughing instantly, causing Blair and everyone else to laugh.

"Okay, how about a little champagne to get the party going" Blair exclaimed, and the girls whooped.

The girls immediately began pouring it, before Blair noticed that Jenny hadn't gotten any. She smirked to herself, enjoying playing with the innocent girl.

"Hey! Jenny didn't get any" Blair said, pretending to be generous.

"Oh, that's okay" Jenny said softly.

"I bet you never had a drink before" Blair said knowingly.

"Oh yes I did, I had some champagne at my cousin's wedding once."

"Ring a ding-ding" Blair said sarcastically.

Kati shoved the glass in her face and the girls all watched her expectantly.

Jenny took a gulp and immediately began to hiccup.

"Hey Jenny, would you like me to pierce your ears for you?" Serena asked. The girls burst into laughter, knowing how bad Serena was at beauty therapy despite her aspirations.

"Isn't that awfully dangerous?" Jenny squeaked.

"No I know what I'm doing, I'm going to be a beautician you know?"

"What's the matter, you afraid?" Blair asked challengingly.

"No I'm not."

"Here S, you can use my virgin pin" Hazel said.

"Nice to know it's good for something" Kati said.

"I don't think this is a good idea, my father won't like it. I promise you and-ARGH" Jenny screamed as Serena tried to pierce the earlobe.

"Why don't we go into the bathroom? My mother will kill me if I get blood all over the carpet"

"What?"

"It'll only bleed for a second."

"Don't worry about it Jenny, if she screws up she can always fix your hair so your ears don't show" Blair said with a smirk.

They quickly entered the bathroom, and a series of screeches could be heard.

Serena emerged from the bathroom not too long after that, claiming that Jenny had gotten sick in the bathroom from the sight of blood.

"Personally I'm getting rather, chilly" Serena said, throwing on a silk robe with an oriental pattern on it.

"Hey what's that?" Blair exclaimed.

"From the ambassador of Korea's son."

The girls screeched in excitement and marveled over Serena's ability to charm so many men at once. Blair was excited for her friend, but couldn't help but feel extremely jealous. The only reason Blair had continued dating Nate for so long was because he was the hottest guy at school and it would make her the most popular. But Blair was yet to believe in love, or perhaps yet to allow herself to believe in it. Now that she was single, it seemed that the attention was off her and onto Serena.

Fed up with the Serena-show, Blair decided to begin a bitch session about Jenny to entertain her minions.

"Miss goody-two-shoes in the bathroom makes me want to barf. Look at me I'm Jenny Humphrey, lousy with virginity. Won't go to bed till I'm legally wed, I can't, I'm Jenny Humphrey." Blair giggled, ignoring the hypocrisy of being a virgin herself. The girls burst into laughter.

"She doesn't drink, or swear. She gets sick from one cigarette" Blair continued, not noticing Jenny opening the door behind her.

"You're making fun of me Blair?"

Blair froze for a second, before regaining her cool.

"Some people are so touchy" Blair snapped.

Outside, the boys had just pulled up in Chuck's limo outside of the Palace hotel where both Chuck and Serena lived. The boys were going to crash Serena's sleep over, via Chuck's idea.

"I changed my mind, let's get out of here" Nate said suddenly, not being able to see Jenny right now without feeling horrible. But the boys weren't budging.

The girls had already spotted them via the window and were squealing.

Blair was shoving clothes on and heading towards the elevator. She had made an unusually sudden decision to go downstairs and wow everybody. It was good to keep the girls and boys on their toes if she wanted to remain queen.

"You goody-goodies are too much for me" she called out, and the girls watched her in shock as she left the sleepover.

"Hey look, there's Waldorf" one of the guys called out once Blair strutted out of the hotel towards the limo. Chuck immediately looked out the window and studied her in interest.

They all stumbled out of the limo to greet her, and Chuck unconsciously fixed his clothes and hair.

"Swell bunch you are, rushing to escort a lady" Blair said with a sarcastic smile. Chuck couldn't keep his eyes off her, silently watching her as he smoked his cigarette.

"Lady? I don't see a lady?" one of the lacrosse players quirked, causing everyone except Chuck and Nate to hoot in laughter. The boys seemed to have lost respect for her since she and Nate broke up, it seemed. Well Blair would show them.

"Shutup" Chuck said coldly, silencing them. Blair and the boys were momentarily shocked.

"What's up Bass?" Blair asked with a smirk, intrigued by his behavior.

"One guess" Chuck said sexily, his dark gaze unwavering.

"You got a lot to offer a girl?" Blair said, surprising herself with how shamelessly she flirted. It just felt natural in that moment.

"Yeah, you know it" Chuck replied huskily, his eyes locked on hers. Blair was utterly captivated, but her nonchalant demeanor and mysterious smile didn't waver. She looked over at Nate to see what he thought about his best friend's flirting.

"What say you Archibald?"

"You're looking good Blair" Nate said, taking a moment out of his brooding to look at her.

"Eat your heart out" Blair said, looking away with a grin as she attempted to look like a heart-breaker.

"Well sloppy seconds aren't my style" Nate said cuttingly, not in the mood for Blair and her games. He started to walk away to catch a cab to his house.

Blair's eyes flashed in anger. She didn't care about Nathaniel Archibald, but she did care about how she looked. And he just made her look bad.

"Where are you going? To flog your log?" she quirked with a triumphant grin, not wanting him to have the last word.

"Well it's better than hanging around with you dorks" Nate called out.

The other guys tried to get Nate to stay, but Chuck had his eyes and attention on Blair and Blair only. He took Nate's departure as his blessing, even though he knew that his friend never really liked Blair to begin with. Chuck on the other hand, had always found Blair fascinating, studying her cool and confident demeanor, her dark beauty and her clever wit from afar. It was about time he explored that.

"Your chariot, my lady" Chuck drawled with a smirk as he opened the door to his limo for her.

Blair turned away from looking at Nate and stared at Chuck. She didn't know what it was. Maybe it was her daring mood, or his sexy charm. But she found herself smiling softly and stepping into his limo.

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**Reviews are welcomed and appreciated :)**


	3. Chapter 3

**So I changed the drag race to a poker game. And Nate is already a jock, so he will be making fun of nerds and bookworms, not jocks. I was tempted to write in a full Chair sex scene but I didn't want to get too AU. I did write how they ended up hooking up though instead of just jumping to them making out in the car like Kenickie and Rizzo did. Also, Chuck Bass would ALWAYS know Blair Waldorf's first name. There was no need for her to tell him what it was.**

**This chapter is M for language and sexual themes.**

**Enjoy!**

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"I don't know what I ever saw in Nate Archibald" Jenny sighed.

"Don't sweat it honey, have one of mine" Serena replied, showing her the long list of guys numbers she had in her cell phone.

"There's so many of them" Jenny exclaimed as she looked through them.

"I know" Serena said with a grin.

"How do you keep up with all of them?"

"I'm a terrific texter. Hopelessly devoted to each and every one" Serena murmured as she typed out a new text.

Meanwhile, Chuck's limo was about to pull away from the curb, filled with Blair and the guys. Chuck reached over to the intercom to speak to his driver.

"Arthur, wait. The gentlemen aren't going to be staying" Chuck said, staring at Blair with a heated look.

"Hey, what are you doing?" they began to protest.

"What do you guys think this is, a gang bang?" Blair snapped, rolling her eyes impatiently.

"You wish" one of guys replied, causing all of them to laugh ridiculously.

"Hit the pavement" Chuck said in a voice of ice, glaring at all of them.

"You've got to be kidding?" Andy Clark said.

"I said now, move it" Chuck snapped. At that, they immediately got out of the limo, yelling out stuff as they exited.

"Alright, alright!"

"Remember us in your will!"

"When a guy picks a chick over his buddies, something's got to be wrong!"

Chuck rolled his eyes and shut the door on them ignoring them. He turned to Blair and his features relaxed instantly as she took in her amused look.

"Come here" Chuck murmured, beckoning her towards him.

"I don't think so Bass" Blair replied, crossing her arms and turning her nose up.

"What made you get in here then Waldorf?" Chuck asked with a knowing smile, but there was curiosity there as well.

"I don't know...clearly a lapse in judgement" Blair retorted, and reached for the door handle to leave, but he moved forward at the speed of light and caught her wrist to stop her. Blair gasped at the heat radiating from his hand on hers, and the rest of his extremely close body nearly pressing against her back. A shiver ran down her spine when she felt his breath on her neck, and she turned around to find his face unexpectedly close to hers. Blair's eyes widened, immediately lost in his dark gaze, not noticing when the limo began to move with her still inside.

The other girls had gone on to do other girly sleep over activities, but Jenny was lost in her own thoughts.

She bit her nail as she pondered over Nate breaking her heart, like many before her. Maybe she also wasn't the first to know that there was just no getting over him. Deep down in her heart, she knew that she was just a fool who was willing to sit around and wait for him. Her head was telling her to forget him, but her heart said to not let go. It told her to hold on till the end, and that was what she intended to do.

Jenny realized right then that she was hopelessly devoted to him. What was she supposed to do now?

Blair had no idea how it had happened. One minute Chuck had been looking at her like she was the most beautiful thing he had ever seen, the next minute her back was pressed against the car door as they made out fiercely. They both let out a series of pleasure-filled moans as their bodies rubbed together.

Chuck was in heaven right now, wrapping his arms, as best he could, around her waist and running his hands all over her perfect figure. She gasped and continued to pant when her lips were released from his, throwing her head back against the window and thrusting her body up rhythmically as he left desperate, wet kisses along the elegant neck that he had been admiring for so long. '_Was this actually happening?_' he thought as he suckled hard enough to leave a mark.

"Mmm Waldorf...Waldorf..._Waldorf_" he groaned against her neck, and Blair grinned with closed eyes at the sound.

"Could you call me by my first name?" Blair breathed out, her voice going unusually soft and vulnerable. She didn't know what came over her, it was like a different person had been living under her skin this whole time and finally came out for him.

Chuck smirked inwardly at her request, but his heart also unexpectedly lifted with the realization that she might care more than he thought. He hardened further at that thought, his next words coming naturally.

"Blair...oh Blair...Blaaaiir" Chuck moaned shamelessly as he grinded against her. Blair didn't anticipate the immensely gratifying feeling surging through her body as she heard him. He said it so desperately and passionately, and it made her feel so incredibly desirable that another shiver went down her spine.

"Thank you" she managed to whisper out right before his lips returned to hers, devouring them.

Blair realized that things were getting hotter and further than she'd ever gone before, but she didn't want to stop. Ever. So she found herself asking "Have you got something?"

Chuck froze, and lifted his head up to stare at her in awe. Blair had been nicknamed the Ice Queen by the boys at St. Jude's once Nate had told them that she wouldn't give it up to him or anyone else for that matter. And Blair wanted this..._him_ to take her right now in his limo.

'What did that mean?' he pondered for a moment in wonder.

He realized that he had been staring at her for quite some time as her noticed how her face started to fill with hesitation.

"Are you kidding?" Chuck drawled, recovering quickly with a confident smirk and Blair grinned in response.

As he leaned back for a moment to retrieve a condom from his wallet, Blair tried to cover her nervousness by shaking out her curls and taking a deep breath.

"My 25 cent insurance policy" Chuck said with a chuckle causing Blair's nerves to disappear as she giggled.

"Big spender" she murmured with a grin, before pressing kisses to the side of his hairline, her hand reaching up to stroke his cheek. Chuck happily enjoyed her attentions for a moment, pleased with her initiating the foreplay.

However the grin fell from his face as he looked at the condom in his wallet. Blair sensed the change in his demeanor instantly.

"What?" Blair asked softly.

"It broke" Chuck stated, not believing that this was happening. Here he was, a billion dollar heir-playboy, and he didn't have a functioning condom in his wallet.

"How could it break?"

"I bought it when I was in the seventh grade" he said, looking away in humiliation.

"Oh" Blair replied, not sure what to do.

Chuck rubbed his forehead, cursing everything under the sun in his head. Blair played with her curls as she thought about it. She couldn't actually lose her virginity in such a risky way could she? But the theme of the night seemed to be risk-taking for her. Blair felt his eyes on her and she turned to find him looking at her with this melting look that made her feel so powerful. Like he would do whatever she wanted. She had to repress another shiver.

"Oh, what the hell" Blair said, before throwing her arms around him in another kiss. There was a little voice in Chuck's head that warned him away from this, but an even louder, possessive voice was telling him that if Blair wanted to take this huge a risk, then he would be the only one taking it with her.

Blair's legs opened of their own accord for Chuck's body to slide in between as they continued to make out. Chuck was about to take it further when there was a heavy bump in their limo. Chuck opened the car roof up to see what the commotion was. Arthur had parked them on a side walk, and Chuck turned around to see Carter Baizen in his Rolls Royce with Georgina Sparks in the passenger seat. He had clearly been behind the bump.

"Hey what the hell do you think you're doing?" Chuck snarled.

"You parked in a no-parking zone, creep," Carter replied, smirking at the lipstick all over Chuck's face.

"The whole place is a no-parking zone, toad face!"

"Oh yeah?"

"Yeah!"

Carter bumped the limo with his car again, leaving a scratch.

"You're going to pay for that" Chuck said in a lethal tone.

"Yeah well, I'll give you 75 cents for the whole car, including your chick!" He retorted, then sped off cackling in laughter with Georgina. Chuck threw his packet of cigarettes after them in anger.

The next day, Chuck and his friends examined the scratch on his limo.

"Nothing a paint job won't fix" Chuck sighed.

"The problem isn't in the scratch, the problem is the fact that it's a _limo_ that someone _else_ is driving for you" Keith Nelson said with a laugh.

"The problem is in your mouth" Chuck replied coldly.

"Hey big stuff, what do you drive?" Nate asked, defending his friend.

"I drive" Keith said defiantly.

"Yeah? How about the rest of you?" Nate asked all of them. They all stuttered, unable to form an answer.

"That's what I thought. Now come on guys, this car could be a major piece of machinery" Nate said brightly.

"Keep talking" Chuck said, interested.

"It could be greased lightning. We'll get lots of tit, the chicks will _cream_" Nate exclaimed. The guys had to perk up at that.

"He's not bragging, it's a real pussy wagon" Chuck continued. They all chuckled and agreed, slapping Chuck on the back.

Weeks later, everyone was at Butter, their usual hang out spot. Chuck was standing with Nate outside when they witnessed Carter and his gang of thugs speed past, nearly running several people over. Chuck couldn't wait to go to one of Baizen's poker games and take him down. He had even sent it in to Gossip Girl so that everyone would know.

"Baizen is asking for it" Chuck said as he took a drag from his cigarette. When Nate didn't reply Chuck looked at him to find him staring at the ground with a broody look on his face.

"Hey what's up Nate, you still thinking about that chick?" Chuck asked, sounding almost understanding, perhaps it was because he actually did understand. He couldn't stop thinking about Blair and when he would see her next. After he had taken her virginity in his limo, their affair had continued via clandestine meetings in classrooms, the limo and each other's houses when they were home alone. While there had been rumors about them, no one knew the exact truth about the nature of their relationship. Chuck and Blair didn't even know.

"What are you, nuts?" Nate exclaimed defensively.

"Well, no. I was just thinking-"

"Get in there, don't think so much" Nate said in his easygoing way, shoving Chuck towards the entry to Butter.

They entered the place and immediately joined their usual gang from St Jude's. Nate spotted Jenny, but she wasn't alone. He felt a strange weight in his chest as he watched her on a date with some nerdy looking guy. Nate quickly looked away when she glanced up at him, and sat down with his back toward her.

Chuck was approached by Dan Humphrey surprisingly.

"You know what I heard? Last year the cops invaded Baizen's poker game and arrested everyone for possession of drugs and guns, and underage gambling" Dan said in a warning tone.

"So? Nobody will catch Chuck Bass" he replied.

"Yeah?"

"Yeah" Chuck said in a final tone, glaring at him. Nobody had noticed Nate glancing at Jenny over his shoulder the entire time, except for Blair who was slowly approaching the boys, martini in hand.

"Somebody making you jealous, Nate?" Blair said as she took a sip of her drink, catching all of the boys at the table's attention.

"Oh bite the weenie, Waldorf" Nate snapped, nervously. Blair smirked in response.

"With relish" she replied, biting her tongue and flashing it to them. Chuck nearly died on the spot, giving her a once-over as he blew out the smoke from his cigarette. He had to touch her in that moment, so when she walked past he reached out and groped her bottom. To everyone's surprise, she didn't get angry, but instead ran her hand through Chuck's hair affectionately and kept walking. What had happened to Blair Waldorf?

"I don't know about these chicks man" Nate said.

"Yeah, they're only good for one thing" Chuck replied with a boyish grin.

"Then what are you supposed to do with them for the other 23 hours and 45 minutes of the day?" Keith Nelson said with a laugh.

"Is that all it takes, 15 minutes?" Dan asked with interest, and they all threw their napkins at him. Chuck pinched his cheek mockingly, causing Dan to roll his eyes and walk away.

"Want something to drink?" Jenny asked her date with a fake smile. Her brother had introduced her to him from his book club at school. She was incredibly bored and he was really dull, but he was nice and wouldn't break her heart like _certain_ other people.

"Sure" he replied, stuffing some money into her hand.

She walked past Nate's table without a glance in their direction, but all of the boys looked up in interest, one of them whistling.

"I'll be right back" Nate said, before walking to the bar where Jenny was, in the opposite direction.

"Hi Nate" Penelope said, throwing herself at Nate. Jenny glanced at them, noticing this.

"I can't talk to you right now" Nate replied, trying to remove her hands as he glanced at Jenny.

"Listen, what are you doing later?" she continued flirtatiously.

"I can't talk, all right?"

"Call me!" She called after him with a giggle.

Nate approached the bar, not standing next to Jenny immediately in an attempt to look casual. He sauntered over to her not too long after.

"Hi Jenny" he said with a nervous smile. She looked up at him with her blue eyes that looked uninterested.

"Oh, hi"

"How are you?" Nate asked, unable to keep the smile off his face as he looked at her.

"Fine thanks" she said, looking for the bar tender with her drink.

"That's good," he said with a pause, "hey Jenny, I've been wanting to talk to you for a long time now."

"What about?" Jenny asked in an unaffected tone.

"Well about that night at Kiss on the Lips. I mean the way I acted, that was terrible. I mean it really was. I mean, it wasn't me, you've got to know that. I mean it was me, of course, but it wasn't me... You see Jenny, I've got this image, right. I've got this-" he rambled, trying to get his explanation out there and failing.

"Well that's why I'm so glad that Tom's such a simple person" Jenny interrupted impatiently, looking at her date and giving him a little wave.

"Simple's right. Too bad that all he has are his brains" Nate replied, chuckling.

"Jealous are you?" she replied with a knowing smile.

"Jealous? Oh come on Jenny, don't make me laugh" Nate said with a goofy laugh.

"And what have you ever done?" she asked challengingly.

"Oh, come on! I can beat that guy in any test" he exclaimed.

"I'll believe that when I see it" Jenny replied in a smug tone, then walked off with her drink, leaving Nate to blink as he stared after her.

* * *

**Hey if you're reading this, can you please let me know in a review or by following the story? I just need to know if it's worth continuing it!**


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